A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin - Sorbonne Université Access content directly
Journal Articles Organic Letters Year : 2005

A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin

Abstract

A chemo-and stereoselective palladium-catalyzed amination of silylated butenediol dicarbonates has allowed for the introduction of a glycine moiety to obtain the desired functionalized epoxysilane. A stereoselective aldolization then delivered the piperidine ring which may be used as a precursor for the synthesis of a variety of polyhydroxylated azasugars. This efficient approach has been illustrated by the synthesis of 1-deoxymannojirimycin including a stereoselective reduction with LAH and a Tamao−Fleming oxidation of a C−SiMe2Ph bond.
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Dates and versions

hal-04227430 , version 1 (03-10-2023)

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Cécile Boglio, Sebastian Stahlke, Serge Thorimbert, Max Malacria. A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin. Organic Letters, 2005, 7 (22), pp.4851-4854. ⟨10.1021/ol051745i⟩. ⟨hal-04227430⟩
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